At some point our signals will be too weak for anyone to pick up or distinguish from cosmic background noise, which probably limits the radius of the sphere of stars that can hear us, but anyone inside that sphere gets at least 80 years to be listening to potentially hear us.
So, even if civilizations only last for say 100 years on average, and you can only hear other civilizations within N light years, if N is big enough eventually someone should hear someone, and if N is really big enough, somewhere in that 100 years everyone should hear at least one other someone.
The largest radio telescope we have (the 305 meter diameter Arecibo) would need to have it's sensitivity increased by around two orders of magnitude JUST to pick up our TV/FM/AM signals from outside the solar system. If we move into the narrowband signals then, depending on the source-strength, it could pick up signals at up to a few thousand light years... if it happened to be pointed in exactly the right direction at exactly the right time.
You'd have to build an absolutely monstrous dish to be able to detect any of our signals at even the center of our own galaxy (much less at the other end)... I haven't run the numbers on it, but I doubt it's physically possible to build a receiver large enough. Add to that that they're highly directional devices and I think you'll find the "N" in your scenario is actually a startlingly small number.
At least they do in my optimistic viewpoint.
A resource crunch, i.e. we simply use up the required resources before we figure out how to explore our planetary neighbourhood. e.g When we figure out that a helium engine is possible, very efficient and very safe, we no longer have sufficient quantities left.